Director, Technical Delivery

Company Details

Company URL: https://www.berkleytechnologyservices.com/                                        

W.R. Berkley Corporation is comprised of 60+ businesses alongside Berkley Technology Services (BTS) and other shared services groups.

Here at Berkley Technology Services, the core of our success is our people. Our teams bring their own unique perspective and experiences which enables us to translate the needs of our business to deliver adaptable, secure solutions while providing an unmatched user-focused experience.

Our tagline “Thoughtful Minds | Empowering Possibilities” was crafted with our own teams in mind. At BTS, our teams thrive in Berkley’s decentralized model - leveraging the power of being part of a long standing, heritage brand with extensive expertise while innovation and being entrepreneurial is encouraged.

Internally, we operate as a relatively flat organization valuing communication and feedback. We pride ourselves in an open-door policy where no one is treated differently based on title, fostering a culture of trust, transparency, and engagement.

Mission (what we stand for):  We Believe in the value of every voice, Translate needs into capabilities, & Secure the future of Berkley. 

Vision (where we’re going): Be the foundation of Berkley through adaptable solutions, resilient environments, and an unmatched experience.

Come join us as we push forward into the future of industry leading technological solutions.

Responsibilities

We are seeking a strategic and results-driven Director of Technical Delivery to lead delivery across our infrastructure and service management organizations. This role is responsible for overseeing a team of technical project managers, ensuring the successful execution of programs and projects across the enterprise. The ideal candidate will bring deep expertise in agile delivery, infrastructure technologies, and cross-functional leadership.  This role requires a strategic thinker with a passion for team development and a commitment to transparent, empowering leadership.

Leadership & Strategy:

• Lead, mentor, and develop a high-performing team of Scrum Masters and Technical Project Managers.
• Define and drive the technical delivery strategy for infrastructure initiatives, aligning with organizational goals.
• Foster a culture of continuous improvement, collaboration, and accountability.Act as a strong advocate for professional development, fostering a culture of continuous learning and skill advancement. Support team members in identifying growth opportunities and aligning them with organizational goals.
• Lead with clarity, empathy, and transparency. Promote open communication, provide regular feedback, and create a psychologically safe environment where team members feel heard, supported, and motivated to excel.

Program & Project Oversight:

• Oversee the planning, execution, and delivery of complex infrastructure projects (e.g., data center migrations, cloud transformations, network upgrades).
• Ensure projects are delivered on time, within scope, and within budget.
• Manage risks, dependencies, and escalations across multiple workstreams.

Delivery Excellence:

• Champion agile methodologies and best practices across infrastructure and service management teams.
• Standardize delivery frameworks and metrics to ensure consistency and transparency.
• Facilitate agile ceremonies and ensure alignment between product, engineering, and operations.
• Demonstrate hands-on experience managing projects using both Waterfall and Agile methodologies, including the ability to navigate and integrate both approaches simultaneously across cross-functional teams.
• Lead the establishment of standardized delivery practices that drive consistency, foster accountability, and elevate team performance.

Stakeholder Management:

• Collaborate with senior leadership, engineering, security, and business stakeholders to prioritize and deliver infrastructure capabilities.
• Communicate project status, risks, and outcomes to executive leadership
• Continue to evolve and optimize Service Now tool.

.

Operational Efficiency:

• Implement tools and processes to improve delivery velocity and quality.
• Track and report on KPIs, OKRs, and delivery health metrics.

Qualifications

• 10+ years of experience in technical project/program delivery, with at least 5 years in a leadership role.
• Proven experience managing infrastructure-related projects (e.g., cloud, networking, server, storage, compute).
• Strong understanding of Agile, Scrum, and Kanban methodologies.
• Deep experience with tools such as Jira, Confluence, ServiceNow, and project portfolio management platforms.
• Excellent communication, leadership, and stakeholder management skills.
• PMP, CSM, SAFe, or equivalent certifications are a plus.
• Bachelors Degree in Computer Science, Information Technology, Information Systems, or a related discipline. Equivalent experience and/or alternative qualifications will be considered.

Preferred Attributes

• Experience in a hybrid or multi-cloud environment (AWS, Azure, GCP).
• Familiarity with ITIL practices and service delivery models.
• Ability to thrive in a fast-paced, matrixed organization.

Behavioral Core Competencies

• Flexibility
• Customer Service Oriented & Operational Effectiveness
• Personal Ownership
• Quick Decision Making
• Team Builder
• Transformational Leadership

 The Company is an equal employment opportunity employer.

Responsibilities

We are seeking a strategic and results-driven Director of Technical Delivery to lead delivery across our infrastructure and service management organizations. This role is responsible for overseeing a team of technical project managers, ensuring the successful execution of programs and projects across the enterprise. The ideal candidate will bring deep expertise in agile delivery, infrastructure technologies, and cross-functional leadership.  This role requires a strategic thinker with a passion for team development and a commitment to transparent, empowering leadership.
 
Leadership & Strategy:
- Lead, mentor, and develop a high-performing team of Scrum Masters and Technical Project Managers.
- Define and drive the technical delivery strategy for infrastructure initiatives, aligning with organizational goals.
- Foster a culture of continuous improvement, collaboration, and accountability.Act as a strong advocate for professional development, fostering a culture of continuous learning and skill advancement. Support team members in identifying growth opportunities and aligning them with organizational goals.
- Lead with clarity, empathy, and transparency. Promote open communication, provide regular feedback, and create a psychologically safe environment where team members feel heard, supported, and motivated to excel.
 
Program & Project Oversight:
- Oversee the planning, execution, and delivery of complex infrastructure projects (e.g., data center migrations, cloud transformations, network upgrades).
- Ensure projects are delivered on time, within scope, and within budget.
- Manage risks, dependencies, and escalations across multiple workstreams.
 
Delivery Excellence:
- Champion agile methodologies and best practices across infrastructure and service management teams.
- Standardize delivery frameworks and metrics to ensure consistency and transparency.
- Facilitate agile ceremonies and ensure alignment between product, engineering, and operations.
- Demonstrate hands-on experience managing projects using both Waterfall and Agile methodologies, including the ability to navigate and integrate both approaches simultaneously across cross-functional teams.
- Lead the establishment of standardized delivery practices that drive consistency, foster accountability, and elevate team performance.
 
Stakeholder Management:
- Collaborate with senior leadership, engineering, security, and business stakeholders to prioritize and deliver infrastructure capabilities.
- Communicate project status, risks, and outcomes to executive leadership
- Continue to evolve and optimize Service Now tool.
.
Operational Efficiency:
- Implement tools and processes to improve delivery velocity and quality.
- Track and report on KPIs, OKRs, and delivery health metrics.